WO2020019278A1 - Composition à base d'époxy en deux parties - Google Patents

Composition à base d'époxy en deux parties Download PDF

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Publication number
WO2020019278A1
WO2020019278A1 PCT/CN2018/097342 CN2018097342W WO2020019278A1 WO 2020019278 A1 WO2020019278 A1 WO 2020019278A1 CN 2018097342 W CN2018097342 W CN 2018097342W WO 2020019278 A1 WO2020019278 A1 WO 2020019278A1
Authority
WO
WIPO (PCT)
Prior art keywords
based composition
epoxy based
general formula
epoxy
composition according
Prior art date
Application number
PCT/CN2018/097342
Other languages
English (en)
Inventor
Bin Li
Chao Wang
Chunfu Chen
Aifu CHE
Original Assignee
Henkel Ag & Co. Kgaa
Henkel (China) Co., Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Henkel Ag & Co. Kgaa, Henkel (China) Co., Ltd. filed Critical Henkel Ag & Co. Kgaa
Priority to JP2021504389A priority Critical patent/JP7252314B2/ja
Priority to PCT/CN2018/097342 priority patent/WO2020019278A1/fr
Priority to CN201880095975.3A priority patent/CN112469757B/zh
Priority to EP18927348.5A priority patent/EP3830169A4/fr
Priority to TW108124193A priority patent/TWI822810B/zh
Publication of WO2020019278A1 publication Critical patent/WO2020019278A1/fr
Priority to US17/153,027 priority patent/US11866535B2/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C08F283/10—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers containing more than one epoxy radical per molecule
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/14—Polycondensates modified by chemical after-treatment
    • C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
    • C08G59/1477—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/44—Amides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/50—Amines
    • C08G59/54—Amino amides>
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
    • C09J163/10—Epoxy resins modified by unsaturated compounds

Definitions

  • This invention relates to a two-part epoxy based composition, comprising a first part comprising at least one epoxy resin; a second part comprising at least one epoxy resin curing agent, and at least one acrylamide compound containing a hydrogen atom bound to the nitrogen atom in the acrylamide structure.
  • the two-part epoxy based composition according to the present invention exhibits excellent adhesion strength to low surface tension substrates, such as stainless steel and PVC.
  • Low surface tension substrates such as stainless steel and polyvinyl chloride (PVC)
  • PVC polyvinyl chloride
  • the low surface tension substrates may need to be attached together or to be bonded with other materials.
  • the existing adhesives however, have trouble to make intimate contact with the surface of the low surface tension substrates and therefore, the low surface tension substrates are not easily bonded.
  • low surface tension substrates need to be mechanically attached or solvent welded because adhesive bonding did not work well with these materials.
  • mechanical attachments such as clips and screws, can cause stress concentrations which may result in cracking and premature failures of the low surface tension substrates.
  • Solvent welding has the problem of relying on the use of hazardous and noxious solvents which is undesirable for the health of workers.
  • Surface modification is an alternative way to bond low surface tension substrates.
  • Techniques such as flame, plasma treatment, and acid etching, are able to change the chemical composition of the surface to increase the surface energy, so that it will be easier for adhesives to flow out on or wet the treated surface and make a suitable bond.
  • the additional surface modification step is costly and adds the complexity of the application of low surface tension substrates.
  • the present invention relates to a two-part epoxy based composition, comprising:
  • R 1 , R 2 and R 3 are identical or different, and independently represent hydrogen atoms, or optionally substituted univalent organic groups;
  • R 2 and R 3 is a hydrogen atom.
  • the two-part epoxy based composition of the invention exhibits high bonding strength to low surface tension substrates, such as PVC and stainless steel.
  • the present invention also relates to a cured product of the two-part epoxy based composition.
  • the present invention also relates to an article bonded by the two-part epoxy based composition.
  • organic group refers to a group that includes at least one carbon atom.
  • exemplary of the organic group includes but not limited to an alkyl group, such as methyl, ethyl, propyl, butyl, pentyl, hexyl, isopropyl, tertiary butyl, isobutyl, chloromethyl, 3, 3, 3-trifluoropropyl and the groups alike; an alkenyl group, such as vinyl, allyl, butenyl, pentenyl, hexenyl and the groups alike; an aralkyl group, such as benzyl, phenethyl, 2- (2, 4, 6-trimethylphenyl) propyl and the groups alike; or an aryl group, such as phenyl, tolyl, xyxyl and the groups alike; an amino group, such as methylamino, dimethylamino, diethylamino, dibenzylamino and the groups alike; and an alk
  • tertiary amino group refers an amino group in which the nitrogen atom is bound to three organic groups, such that two of these groups together may also be part of a ring.
  • the first part of the present invention comprises at least one epoxy resin.
  • the epoxy resin of the first part refers to any common epoxy resin containing at least one epoxy group per molecule, and preferably containing multiple epoxy groups per molecule.
  • Exemplary of the epoxy resin includes but not limited to bisphenol A epoxy resins, bisphenol F epoxy resins, biphenyl epoxy resins, naphthalene epoxy resins, diphenyl ether epoxy resins, diphenyl thioether epoxy resins, hydroquinone epoxy resins, biphenyl novolac epoxy resins, cresol novolac epoxy resins, phenol novolac epoxy resins, bisphenol A novolac epoxy resins, trisphenol epoxy resins, tetraphenylolethane epoxy resins, and any combination thereof.
  • Examples of commercially available epoxy resin are, for example, D. E. R. 331 from Olin Corporation; EPON 828 from Shell Chemical Corporation; and EPICLON N-665 from Dainippon Ink and Chemicals Inc.
  • the amount of the epoxy resin in the first part is from 20 to 100%, preferably from 50 to 90%, and more preferably from 80 to 90%by weight based on the total weight of the first part.
  • the first part of the present invention may optionally further comprise additives, such as at least one first filler.
  • the first filler may be an organic filler, an inorganic filler and the combination thereof.
  • the first filler may function as a structural reinforcement component, a thermally conducting component, an electrically conducting component, and an adhesion promoting component.
  • Suitable first filler includes but not limited to silica, alumina, zinc oxide, boron nitride, glass fibers and the likes. Examples of commercially available first fillers are, for example, TS720 from Cabot; and Aerosil R202 from Evonik.
  • the amount of the first filler in the first part is from 0 to 80%, preferably from 0 to 50%, and more preferably from 10 to 20%by weight based on the total weight of the first part.
  • the second part of the present invention comprises at least one epoxy resin curing agent.
  • the epoxy curing agent of the second part refers to any commonly used curing agent for epoxy systems, and includes but not limited to polyamide, amine, imidazole and the derivatives thereof.
  • Illustrative curing catalysts include polyamide resin based on dimerized fatty acid and polyamines, methyldiethanolamine, triethanolamine, diethylaminopropylamine, benzyldimethyl amine, m-xylylenedi (dimethylamine) , benzyldimethylamine, 2, 4, 6-tris (dimethylaminomethyl) phenol, 1-methylimidazole, 2-methylimidazole and 2, 4-diethylimidazole.
  • Examples of commercially available epoxy curing agent are Versamid 140 from Gabriel Performance Products; Ancamine TEPA from Evonik; Ajicure PN-H from Ajinomoto Fine-Techno Co., Ltd.; Fujicure-FXR-1090FA from T&K Toka; 1, 2-dimethyl imidazole from Shikoku Chemicals Corporation; 2E4MI, from Evonik; and Gaskamine 240 from Mitsubishi Gas Chemical.
  • the amount of the epoxy curing agent in the second part is from 5 to 75%, preferably from 10 to 70%, and more preferably from 10 to 50%by weight based on the total weight of the second part.
  • the second part of the present invention also comprises at least one acrylamide compound represented by the following general formula (1) :
  • R 1 , R 2 and R 3 are identical or different, and independently represent hydrogen atoms, or optionally substituted univalent organic groups; and at least one of R 2 and R 3 is a hydrogen atom. Not binding by any theory, it is believed that the hydrogen atom which is bound to the nitrogen atom in the acrylamide structure in the general formula (1) reacts with the epoxy ring in the epoxy resin and therefore helps the curing of the two-part epoxy based composition.
  • At least one of R 1 , R 2 and R 3 in the general formula (1) contains a tertiary amino group. More preferably, at least one of R 2 and R 3 in the general formula (1) contains a tertiary amino group. Not binding by any theory, it is believed that the tertiary amino group functions to catalyze the curing of the epoxy resin, and therefore further helps the curing of the two-part epoxy based composition.
  • R 1 , R 2 and R 3 in the general formula (1) is a group represented by the following general formula (2) :
  • R 4 and R 5 are identical or different, and independently represent hydrogen atoms, and optionally substituted univalent organic groups; a is an integer from 1 to 20, and preferably from 1 to 10. More preferably, R 4 and R 5 in the general formula (2) are optionally substituted C 1 to C 6 univalent organic groups, such as methyl, ethyl and vinyl groups.
  • acrylamide compound of the present invention are:
  • Examples of commercially available acrylamide compound represented by the general formula (1) are Visiomer DMAPMA from Evonik; and DMAPMA from Feixiang Group of Companies.
  • the amount of the acrylamide compound represented by the general formula (1) in the second part is from 25 to 95%, preferably from 30 to 90%, and more preferably from 50 to 70%by weight based on the total weight of the second part.
  • the second part of the present invention may optionally further comprise additives, such as at least one coupling agent, and at least one second filler.
  • the coupling agent of the present invention may be any common coupling agent known in the art.
  • the coupling agent may be selected from a silane coupling agent, a titanate coupling agent, or the like.
  • the coupling agent of the present invention can be used alone or in combination.
  • the silane coupling agent can be exemplified by epoxy-containing alkoxysilane, such as 3 -glycidoxypropyl trimethoxysilane, 3 -glycidoxypropyl methyldiethoxysilane, and 3 -glycidoxypropyl triethoxysilane; amino-containing alkoxysilane, such as gamma-aminopropyl trimethoxysilane, gamma-aminopropyl triethoxysilane, gamma-aminopropyl triisopropoxysilane, and gamma-aminopropylmethyl dimethoxysilane; and mercapto-containing alkoxysilane, such as 3-mercaptopropyl trimethoxysilane.
  • epoxy-containing alkoxysilane such as 3 -glycidoxypropyl trimethoxysilane, 3 -glycidoxypropyl methyldiethoxysilane,
  • the titanate coupling agent can be exemplified by i-propoxytitanium tri (i-isostearate) .
  • i-propoxytitanium tri i-isostearate
  • Examples of commercially available coupling agents are, for example, KMB403, KMB 603 from Shin-Etsu Chemical; SILQUEST A187, SILQUEST A1120 from Momentive; and GENIOSIL GF9 from Wacker Chemie AG.
  • the amount of the second filler in the second part is from 0 to 80%, and preferably from 0 to 50%by weight based on the total weight of the second part.
  • the second filler of the present invention may be the same or different from the first filler.
  • the second filler may be an organic filler, an inorganic filler and the combination thereof.
  • the second filler may function as a structural reinforcement component, a thermally conducting component, an electrically conducting component, and an adhesion promoting component.
  • Suitable second filler includes but not limited to silica, alumina, zinc oxide, boron nitride, glass fibers and the likes. Examples of commercially available second fillers are, for example, TS720 from Cabot; and Aerosil R202 from Evonik.
  • the amount of the second filler in the second part is from 0 to 80%, and preferably from 0 to 50%by weight based on the total weight of the second part.
  • the two-part epoxy based composition comprises:
  • R 1 represents a hydrogen atom or an optionally substituted C 1 to C 6 univalent organic group
  • R 2 and R 3 are hydrogen atom, and the other one of R 2 and R 3 is a group represented by the following formula (2) ,
  • R4 and R5 are identical or different, and independently represent optionally substituted C 1 to C 6 univalent organic groups; and a is an integer from 1 to 10.
  • the first part should be used in a weight ratio to the second part, in the range of 20: 1 to 1: 1, preferably from 10: 1 to 1.5: 1, and more preferably from 2: 1 to 1.5: 1.
  • a person skilled in the art will be able to make appropriate choices among the varies components based on the description, representative examples and guidelines of the present invention to prepare a composition to achieve desired effects.
  • the first part and the second part should be combined 10 to 30 minutes prior to the use of the two-part epoxy based composition for substrate bonding.
  • the two-part epoxy based composition of the present invention may be prepared by:
  • R 1 , R 2 and R 3 are identical or different, and independently represent hydrogen atoms, or optionally substituted univalent organic groups; and at least one of R 2 and R 3 is a hydrogen atom.
  • the two-part epoxy based composition of the present invention may be cured in a temperature range from 20 to 80°C and applied to substrates by a mixing gun.
  • the lap shear strength of the two-part epoxy based composition of the present invention may be assessed according to ASTM D 1002.
  • the two-part epoxy based composition of the present invention preferably has a lap shear strength greater than or equal to 2 Mpa, and more preferably greater than or equal to 5 Mpa after being applied to rigid PVC.
  • the two-part epoxy based composition of the present invention preferably has a lap shear strength greater than or equal to 4 Mpa, and more preferably greater than or equal to 5 Mpa after being applied to stainless steel.
  • a first part of the two-part epoxy based composition sample was prepared according to Table 1A by obtaining difunctional bisphenol A/epichlorohydrin derived liquid epoxy resin (Epon 828, from Momentive) ;
  • a second part of the two-part epoxy based composition sample was prepared according to Table 1B by mixing polyamide resin (Versamid 140, from Gabriel Performance Products) , tetraethylene pentamine (Ancamine TEPA, from Evonik) , and N- [3- (dimethylamino) propyl] -2-methacrylamide (Visiomer DMAPMA, from Evonik) .
  • the first part and the second part of the two-part epoxy based composition sample were mixed in a weight ratio of 1.9: 1 and were mixed together 20 minutes before the lap shear strength test was conducted.
  • the two-part epoxy based composition sample was cured at room temperature.
  • a first part and a second part of the two-part epoxy based composition sample were prepared in the same way as in Example 1, according to Table 1A and 1B.
  • the first part and the second part of the two-part epoxy based composition sample were mixed in a weight ratio of 1.8: 1 and were mixed together 20 minutes before the lap shear strength test was conducted.
  • the two-part epoxy based composition sample was cured at room temperature.
  • a first part and a second part of the two-part epoxy based composition sample were prepared in the same way as in Example 1, according to Table 1A and 1B.
  • the first part and the second part of the two-part epoxy based composition sample were mixed in a weight ratio of 1.8: 1 and were mixed together 20 minutes before the lap shear strength test was conducted.
  • the two-part epoxy based composition sample was cured at room temperature.
  • a first part and a second part of the two-part epoxy based composition sample were prepared in the same way as in Example 1, according to Table 1A and 1B.
  • the first part and the second part of the two-part epoxy based composition sample were mixed in a weight ratio of 1.7: 1 and were mixed together 20 minutes before the lap shear strength test was conducted.
  • the two-part epoxy based composition sample was cured at room temperature.
  • a first part and a second part of the two-part epoxy based composition sample were prepared in the same way as in Example 1, according to Table 1A and 1B.
  • N N-dimethyl acrylamide (DMAA, from Eastman) was used instead of N- [3- (dimethylamino) propyl] -2-methacrylamide (Visiomer DMAPMA, from Evonik) .
  • the first part and the second part of the two-part epoxy based composition sample were mixed in a weight ratio of 1.27: 1 and were mixed together 20 minutes before the lap shear strength test was conducted.
  • the two-part epoxy based composition sample was cured at room temperature.
  • a first part and a second part of the two-part epoxy based composition sample were prepared in the same way as in Example 1, according to Table 1A and 1B.
  • the first part and the second part of the two-part epoxy based composition sample were mixed in a weight ratio of 1.9: 1 and were mixed together 20 minutes before the lap shear strength test was conducted.
  • the two-part epoxy based composition sample was cured at room temperature.
  • a first part and a second part of the two-part epoxy based composition sample were prepared in the same way as in Example 1, according to Table 1A and 1B. No N- [3- (dimethylamino) propyl] -2-methacrylamide (Visiomer DMAPMA, from Evonik) was incorporated in the two part epoxy based composition sample.
  • the first part and the second part of the two-part epoxy based composition sample were mixed in a weight ratio of 2: 1 and were mixed together 20 minutes before the lap shear strength test was conducted.
  • the two-part epoxy based composition sample was cured at room temperature.
  • the lap shear strength of the two-part epoxy based composition was determined according to ASTM D 1002, and the two part epoxy based composition tested had a thickness of 0.127mm between the testing samples of rigid PVC panels or 301 stainless steel panels.
  • MTS Criterion Model 43 was used for this test procedure.
  • Example 1 Example 2 Example 3 Example 4 Lap shear strength (Mpa) 5.53 4.98 4.75 0.76

Abstract

La présente invention concerne une composition à base d'époxy en deux parties, comprenant une première partie comprenant au moins une résine époxy ; une seconde partie comprenant au moins un agent de durcissement de résine époxy, et au moins un composé acrylamide contenant un atome d'hydrogène lié à l'atome d'azote dans la structure acrylamide. La composition à base d'époxy en deux parties selon la présente invention présente une excellente force d'adhérence à des substrats à faible tension de surface, tels que l'acier inoxydable et le PVC.
PCT/CN2018/097342 2018-07-27 2018-07-27 Composition à base d'époxy en deux parties WO2020019278A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
JP2021504389A JP7252314B2 (ja) 2018-07-27 2018-07-27 ２剤型エポキシ系組成物
PCT/CN2018/097342 WO2020019278A1 (fr) 2018-07-27 2018-07-27 Composition à base d'époxy en deux parties
CN201880095975.3A CN112469757B (zh) 2018-07-27 2018-07-27 基于环氧化物的两部分组合物
EP18927348.5A EP3830169A4 (fr) 2018-07-27 2018-07-27 Composition à base d'époxy en deux parties
TW108124193A TWI822810B (zh) 2018-07-27 2019-07-10 基於兩部份環氧樹脂的組合物
US17/153,027 US11866535B2 (en) 2018-07-27 2021-01-20 Two-part epoxy based composition

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/CN2018/097342 WO2020019278A1 (fr) 2018-07-27 2018-07-27 Composition à base d'époxy en deux parties

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US17/153,027 Continuation US11866535B2 (en) 2018-07-27 2021-01-20 Two-part epoxy based composition

Publications (1)

Publication Number Publication Date
WO2020019278A1 true WO2020019278A1 (fr) 2020-01-30

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Application Number Title Priority Date Filing Date
PCT/CN2018/097342 WO2020019278A1 (fr) 2018-07-27 2018-07-27 Composition à base d'époxy en deux parties

Country Status (6)

Country Link
US (1) US11866535B2 (fr)
EP (1) EP3830169A4 (fr)
JP (1) JP7252314B2 (fr)
CN (1) CN112469757B (fr)
TW (1) TWI822810B (fr)
WO (1) WO2020019278A1 (fr)

Citations (2)

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Publication number Priority date Publication date Assignee Title
US20030004296A1 (en) * 2001-05-16 2003-01-02 Ajinomoto Co., Inc. Latent curing agent for epoxy resin, and curable epoxy resin composition
CN101412896A (zh) * 2007-10-17 2009-04-22 比亚迪股份有限公司 一种双组分环氧树脂粘合剂及其制备方法

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US3878247A (en) * 1974-01-25 1975-04-15 Jefferson Chem Co Inc Preparation of n-(tertiaryaminoalkyl) acrylamides
US4188474A (en) * 1978-09-11 1980-02-12 Texaco Development Corporation Epoxy curing accelerator
JPS6429466A (en) * 1987-07-25 1989-01-31 Kansai Paint Co Ltd Coating resin composition
JP4001677B2 (ja) * 1998-05-27 2007-10-31 日東電工株式会社 熱硬化型接着剤組成物とその接着シ―ト類
CN102159642B (zh) * 2008-07-23 2015-07-22 3M创新有限公司 双组分环氧基结构粘合剂
US8895148B2 (en) 2011-11-09 2014-11-25 Cytec Technology Corp. Structural adhesive and bonding application thereof
JPWO2017169574A1 (ja) * 2016-03-30 2019-02-14 東レ株式会社 感光性接着剤組成物、硬化物、感光性接着剤シート、積層基板および接着剤パターン付積層基板の製造方法

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030004296A1 (en) * 2001-05-16 2003-01-02 Ajinomoto Co., Inc. Latent curing agent for epoxy resin, and curable epoxy resin composition
CN101412896A (zh) * 2007-10-17 2009-04-22 比亚迪股份有限公司 一种双组分环氧树脂粘合剂及其制备方法

Also Published As

Publication number Publication date
JP7252314B2 (ja) 2023-04-04
CN112469757B (zh) 2023-07-14
TWI822810B (zh) 2023-11-21
EP3830169A1 (fr) 2021-06-09
US11866535B2 (en) 2024-01-09
TW202012579A (zh) 2020-04-01
JP2022501451A (ja) 2022-01-06
EP3830169A4 (fr) 2022-03-02
US20210171694A1 (en) 2021-06-10
CN112469757A (zh) 2021-03-09

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